Triethylamine → 4-[(5-Nitro-furan-2-yl)-ethynyl]benzonitrile

HRID 1626Notes

Reaction equation

HRID 1626 reaction equation
Br[C:2]1[O:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][CH:6]=1.C(N(CC)CC)C.[C:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)#[CH:18]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:7]([C:4]1[O:3][C:2]([C:18]#[C:17][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:6][CH:5]=1)([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2335822-Bromo-5-nitrofuranHCID 45472454-Ethynylbenzonitrile

Product 1

HCID 196919514-[(5-Nitro-furan-2-yl)-ethynyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-5-nitrofuran (1.65 g) and triethylamine (34 ml) in anhydrous acetonitrile (55 ml) under nitrogen was added bis(triphenylphosphine)palladium dichloride (130 mg) and cuprous iodide (35 mg). 4-Ethynylbenzonitrile (1.09 g) was added and the reaction mixture was stirred under nitrogen overnight. The mixture was evaporated to dryness and the residue was dissolved in dichloromethane (200 ml), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (ethyl acetate/hexane 1:10) and triturated with ethyl acetate/hexane (1:3) to give 4-[(5-nitro-2-furyl)-ethynyl]benzonitrile.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane (200 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane 1:10)
  7. customtriturated with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-fd2ce529eb5e4230a968d9b7a9207cfc
Source dataset
uspto-grants-1998_03
Patent number
US05726195

Reaction notes

Loading…